Redoxdivergent Construction of (Dihydro)thiophenes with DMSO.

Abstract

Thiophene-based rings are one of the most widely used building blocks for the synthesis of sulfur-containing molecules. Inspired by the redox diversity of nature s feature, we demonstrate herein a redoxdivergent construction of dihydrothiophenes, thiophenes and bromothiophenes respectively from readily available allylic alcohols, dimethyl sulfoxide (DMSO) and HBr. The redoxdivergent selectivity could be manipulated mainly through controlling the dosage of DMSO and HBr. Mechanistic studies suggest that DMSO simultaneously acts as an oxidant and a sulfur donor. The synthetic potentials of the products as platform molecules have also been demonstrated by various derivatizations, including the preparation of bioactive and functional molecules.